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Stereoselective synthesis of the C1–C13 fragment of bistramide A

✍ Scribed by Marie-Aude Hiebel; Béatrice Pelotier; Olivier Piva

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
486 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

The C1-C13 fragment of bistramide A was prepared from 5-hexenoic acid in 15 linear steps and in 16% overall yield. The core 2,6-trans-tetrahydropyran ring was obtained via a kinetically controlled oxa-Michael cyclization from the corresponding chiral a,b-unsaturated hydroxyester. This precursor was prepared by using a diastereoselective alkylation reaction using Davies Superquat auxiliary and a diastereoselective Roush's allylboration as key steps.

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A stereoselective synthesis of the C13C
A stereoselective synthesis of the C13C19 fragment of sanglifehrin A
✍ Mukund K Gurjar; Siddhartha Ray Chaudhuri 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 261 KB

A stereo-controlled radical C C bond formation involving a 5-chloro-5-deoxy-L-idofurano-6,3-lactone derivative and allyltri-n-butyltin/AIBN is described. Further elaboration led to the synthesis of the C13 C19 segment of sanglifehrin A.